Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 4, Problem 4.78P

Read Appendix B on naming bicyclic compounds. Then give IUPAC name for each of the following compounds.

a. Chapter 4, Problem 4.78P, Read Appendix B on naming bicyclic compounds. Then give IUPAC name for each of the following , example  1

b. Chapter 4, Problem 4.78P, Read Appendix B on naming bicyclic compounds. Then give IUPAC name for each of the following , example  2

c. Chapter 4, Problem 4.78P, Read Appendix B on naming bicyclic compounds. Then give IUPAC name for each of the following , example  3

d. Chapter 4, Problem 4.78P, Read Appendix B on naming bicyclic compounds. Then give IUPAC name for each of the following , example  4

Expert Solution
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Interpretation Introduction

(a)

Interpretation: The IUPAC name for the given bicyclic compound is to be stated.

Concept introduction: The root name of bicyclic compounds depends upon the number of carbon atoms present in the rings. The naming of bicyclic compounds is done as,

(1) The total number of carbon atoms in the molecule is to be counted. It represents the root name.

(2) The number of carbon atoms between the bridgeheads is to be counted and placed in square brackets in descending order.

(3) The word bicyclo is placed at the beginning of the name.

The general name such compounds is represented as bicyclo[x.y.z]alkane.

Answer to Problem 4.78P

The IUPAC name for the given bicyclic compound is 2,3dimethylbicyclo[3.1.1]heptane.

Explanation of Solution

The given bicyclic compound is shown below.

Organic Chemistry, Chapter 4, Problem 4.78P , additional homework tip  1

Figure 1

The given compound contains seven carbon atoms in the ring which are single bonded to each other. Therefore, the root name is heptane. In this case, there are 3,1 and 1 carbon atoms present between the bridgehead which are placed in descending order as [3.1.1]. There are two dimethyl groups present at C2 and C3 positions. Hence, the IUPAC name for the given bicyclic compound is 2,3dimethylbicyclo[3.1.1]heptane.

Conclusion

The IUPAC name for the given bicyclic compound is 2,3dimethylbicyclo[3.1.1]heptane.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The IUPAC name for the given bicyclic compound is to be stated.

Concept introduction: The root name of bicyclic compounds depends upon the number of carbon atoms present in the rings. The naming of bicyclic compounds is done as,

(1) The total number of carbon atoms in the molecule is to be counted. It represents the root name.

(2) The number of carbon atoms between the bridgeheads is to be counted and placed in square brackets in descending order.

(3) The word bicyclo is placed at the beginning of the name.

The general name such compounds is represented as bicyclo[x.y.z]alkane.

Answer to Problem 4.78P

The IUPAC name for the given bicyclic compound is 2ethyl7,7dimethylbicyclo[2.2.1]heptane.

Explanation of Solution

The given bicyclic compound is shown below.

Organic Chemistry, Chapter 4, Problem 4.78P , additional homework tip  2

Figure 2

The given compound contains seven carbon atoms in the ring which are single bonded to each other. Therefore, the root name is heptane. In this case, there are 2,2 and 1 carbon atoms present between the bridgehead which are placed in descending order as [2.2.1]. There are two methyl groups present at C7 position and one ethyl group at C2 position. Hence, the IUPAC name for the given bicyclic compound is 2ethyl7,7dimethylbicyclo[2.2.1]heptane.

Conclusion

The IUPAC name for the given bicyclic compound is 2ethyl7,7dimethylbicyclo[2.2.1]heptane.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The IUPAC name for the given bicyclic compound is to be stated.

Concept introduction: The root name of bicyclic compounds depends upon the number of carbon atoms present in the rings. The naming of bicyclic compounds is done as,

(1) The total number of carbon atoms in the molecule is to be counted. It represents the root name.

(2) The number of carbon atoms between the bridgeheads is to be counted and placed in square brackets in descending order.

(3) The word bicyclo is placed at the beginning of the name.

The general name such compounds is represented as bicyclo[x.y.z]alkane.

Answer to Problem 4.78P

The IUPAC name for the given bicyclic compound is 1methyl7propylbicyclo[3.2.1]octane.

Explanation of Solution

The given bicyclic compound is shown below.

Organic Chemistry, Chapter 4, Problem 4.78P , additional homework tip  3

Figure 3

The given compound contains eight carbon atoms in the ring which are single bonded to each other. Therefore, the root name is octane. In this case, there are 3,2 and 1 carbon atoms present between the bridgehead which are placed in descending order as [3.2.1]. There is one propyl group present at C7 position and one methyl group at C1 position. Hence, the IUPAC name for the given bicyclic compound is 1methyl7propylbicyclo[3.2.1]octane.

Conclusion

The IUPAC name for the given bicyclic compound is 1methyl7propylbicyclo[3.2.1]octane.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The IUPAC name for the given bicyclic compound is to be stated.

Concept introduction: The root name of bicyclic compounds depends upon the number of carbon atoms present in the rings. The naming of bicyclic compounds is done as,

(1) The total number of carbon atoms in the molecule is to be counted. It represents the root name.

(2) The number of carbon atoms between the bridgeheads is to be counted and placed in square brackets in descending order.

(3) The word bicyclo is placed at the beginning of the name.

The general name such compounds is represented as bicyclo[x.y.z]alkane.

Answer to Problem 4.78P

The IUPAC name for the given bicyclic compound is 6ethyl3,3dimethylbicyclo[3.2.0]heptane.

Explanation of Solution

The given bicyclic compound is shown below.

Organic Chemistry, Chapter 4, Problem 4.78P , additional homework tip  4

Figure 4

The given compound contains seven carbon atoms in the ring which are single bonded to each other. Therefore, the root name is heptane. In this case, there are 3,2 and 0 carbon atoms present between the bridgehead which are placed in descending order as [3.2.0]. There is one ethyl group present at C6 position and two methyl groups at C3 position. Hence, the IUPAC name for the given bicyclic compound is 6ethyl3,3dimethylbicyclo[3.2.0]heptane.

Conclusion

The IUPAC name for the given bicyclic compound is 6ethyl3,3dimethylbicyclo[3.2.0]heptane.

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Chapter 4 Solutions

Organic Chemistry

Ch. 4 - Problem 4.9 Give the structure corresponding to...Ch. 4 - Prob. 4.12PCh. 4 - Give the IUPAC name for each compound.Ch. 4 - Give the structure corresponding to each IUPAC...Ch. 4 - Arrange the following compounds in order of...Ch. 4 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4 - Prob. 4.17PCh. 4 - a.Draw the three staggered and three eclipsed...Ch. 4 - Problem 4.19 Consider rotation around the...Ch. 4 - Calculate the destabilization present in each...Ch. 4 - Problem 4.21 Classify the ring carbons as up or...Ch. 4 - Draw a second chair conformation for each...Ch. 4 - Prob. 4.23PCh. 4 - Problem 4.25 Draw the structure for each compound...Ch. 4 - For cis-1, 3-diethylcyclobutane, draw a a...Ch. 4 - Prob. 4.26PCh. 4 - Problem 4.28 Consider . Draw structures f or the...Ch. 4 - Problem 4.29 Draw a chair conformation of...Ch. 4 - Prob. 4.29PCh. 4 - Draw the products of each combustion reaction.Ch. 4 - Explain why beeswax is insoluble in H2O, slightly...Ch. 4 - Prob. 4.32PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 - Consider the substituted cyclohexane shown in the...Ch. 4 - Prob. 4.35PCh. 4 - 3.31 For each alkane: (a) classify each carbon...Ch. 4 - Prob. 4.37PCh. 4 - Prob. 4.38PCh. 4 - Give the IUPAC name for each compound. a. h.k....Ch. 4 - 4.39 Give the structure and IUPAC name for each of...Ch. 4 - 4.40 Draw the structure corresponding to each...Ch. 4 - Prob. 4.42PCh. 4 - Prob. 4.43PCh. 4 - 4.42 Give the IUPAC name for each compound. a....Ch. 4 - Prob. 4.45PCh. 4 - Prob. 4.46PCh. 4 - 4.45 Which conformation in each pair is higher in...Ch. 4 - Considering rotation around the bond highlighted...Ch. 4 - Prob. 4.49PCh. 4 - Prob. 4.50PCh. 4 - 4.49 Label the sites of torsional and steric...Ch. 4 - Prob. 4.52PCh. 4 - 4.51 The eclipsed conformation of is less...Ch. 4 - (a) Draw the anti and gauche conformations for...Ch. 4 - For each compound drawn below: a.Label each OH,Br...Ch. 4 - Draw the two possible chair conformations for...Ch. 4 - For each compound drawn below: a. Draw...Ch. 4 - 4.56 Convert each of the following structures into...Ch. 4 - Prob. 4.59PCh. 4 - Prob. 4.60PCh. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 4.62PCh. 4 - Prob. 4.63PCh. 4 - 4.62 Draw the three constitutional isomers having...Ch. 4 - Prob. 4.65PCh. 4 - Prob. 4.66PCh. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Which of the following compounds are lipids?Ch. 4 - Prob. 4.69PCh. 4 - Prob. 4.70PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 4.72PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 4.74PCh. 4 - Prob. 4.75PCh. 4 - Consider the tricyclic structure B (a) Label each...Ch. 4 - Read Appendix B on naming branched alkyl...Ch. 4 - Read Appendix B on naming bicyclic compounds. Then...
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